HR Director, North America & EOR

About Datarails Come build the future of finance with Datarails. We're a global, AI-powered FinanceOS company helping finance teams transform the way they work. By combining intelligent automation, AI, and seamless integrations with the tools finance teams already know and trust, we empower organizations to make faster, smarter decisions with confidence. With approximately 350 employees worldwide, we're building the next generation of finance technology - where innovation, collaboration, and customer success go hand in hand. If you're looking for a fantastic opportunity to join a growing startup in a role with massive impact, we would love to meet you! About the Role We're hiring an HR Director to lead people strategy and operations for our North American and EOR teams. This is a hands-on leadership role. You'll be the go-to HR partner for North American and EOR leaders and employees, own day-to-day HR operations, and work closely with our Israel-based HR and leadership teams to keep policies, programs and culture aligned across both regions. Must be comfortable experimenting with automation and AI tools, and able to work collaboratively with HRIS person in Israel to continuously optimize internal processes and workflows. Location: Fully remote, based in the New York City metro area. You'll need to attend in-person meetings with leadership on short notice, including lunches and occasional offsites when executives visit from Israel. Reports to: Chief Human Resources Officer Team: Manages a two-person People team: a People Operations Generalist and a People & Compliance Manager What You'll Own Team leadership • Lead and develop the North America and EOR People team, covering People experience, operations, policies and compliance. • Set the team's priorities, coach its members, and serve as the regional escalation point for HR issues. Leadership partnership • Serve as the strategic HR partner to C-level leaders on objectives, KPIs and retention. • Partner with VP-level leaders on organizational and people priorities. Organizational and talent planning • Partner closely with senior leadership and the Global Director of Talent Acquisition on team structure planning against company and department goals. Compensation and merit • Own the annual merit cycle end to end, in close collaboration with the HR Director in Israel: planning, execution, and review of salary bands, thresholds and pay equity. • Work with department leaders to evaluate ad-hoc compensation adjustments needed, in close partnership with the People team. Benefits, leave and compliance • Own annual benefits selection and benefits policy. • Own leave policy, including parental, disability, leave of absence and work-from-abroad. • Work closely with People & Compliance Manager on HR compliance audits. People operations and budget • Own the Rippling platform as the North America and EOR HR system of record, working in close collaboration with the HRIS person to keep Rippling and HiBob aligned • Build and manage the People Ops budget. • Oversee travel and Mesh card management. Culture, communications and development • Partner with the Chief of Staff on critical people-focused internal communications • Lead learning and development programs. What You'll Bring • Proven experience directing the HR function at one or more startups or high-growth tech companies, as the senior HR leader for a region or the whole company. • 10+ years of progressive HR experience, including time as a director or head of HR. • Deep working knowledge of U.S. and Canadian employment law and multi-state compliance. • Hands-on command of core HR operations: onboarding and offboarding, HRIS, benefits, payroll partnership, policies and documentation. • Strong employee relations judgment, including investigations, performance management and sensitive exits. • Comfort building process where little exists and doing the work yourself, not only directing it. • Clear, direct communication and the credibility to advise senior leaders. • Based in the New York City metro area. Nice to Have • Experience leading HR for the North American arm of an Israeli-headquartered startup, and comfort working across Israeli and North American business cultures and time zones. • Experience with global HR coordination: aligning U.S. and Canadian policies, benefits and comp practices with a headquarters in another country. • Background in a SaaS or fintech company. • SHRM-SCP, SPHR or equivalent certification. • Experience administering Rippling; familiarity with HiBob is a plus. What We Offer • A collaborative, team-oriented environment, the ability to own your schedule (work your local time zone), and the opportunity to grow at Datarails over many years • Base compensation - The target base salary range will be between $160,000 to $195,000 base salary per year, based on multiple factors including prior experience, and skills. We are open to candidates with varying levels of experience. • Meaningful equity • 401(k) plan with up to 4% match and HSA & FSA Options • 100% paid medical, dental, and vision coverage for employees and 100% paid medical and 80% paid dental and vision coverage for dependents • $540/year toward glasses, sunglasses, or contact lenses from XP Health for employees enrolled in any Guardian Vision plan • Calm app membership • Parental leave • Flexible sick time and PTO (we recommend 18-25 vacation days annually) • 12 paid company holidays • Life insurance • CPA/CFA license renewal reimbursement Notice: We're aware of individuals impersonating Datarails recruiters. All legitimate Datarails recruiting communication comes from an @datarails.com email address or a LinkedIn message from a Datarails employee. If you've received a message claiming to be from Datarails that looks suspicious, please forward it to careers@datarails.com We want to make sure everyone has an equal chance to participate and make a difference. Datarails is an equal opportunity employer and prioritizes building a diverse and inclusive workplace. We provide equal employment opportunities to all employees and applicants of any type and do not discriminate based on race, color, religion, national origin, gender, age, sexual orientation, physical or mental disability, genetic information or characteristic, gender identity and expression, veteran status, or other non-job related characteristics or other prohibited grounds specified in applicable federal, state, and local laws. Datarails’ policy is to comply with all applicable laws related to nondiscrimination and equal opportunity and will not tolerate discrimination or harassment based on any of these characteristics. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.